#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:29:37 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268674 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/30/7243068.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243068
loop_
_publ_author_name
'Singh, Abhishek'
'Singh, Reman Kumar'
'Patwari, G. Naresh'
_publ_section_title
;
 Hierarchy of π-stacking determines the conformational preferences of
 bis-squaramates
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              5331
_journal_page_last               5336
_journal_paper_doi               10.1039/D1CE00623A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C7 H8 N O3'
_chemical_formula_sum            'C14 H16 N2 O6'
_chemical_formula_weight         154.14
_chemical_name_common
4,4'-(butane-1,4-diylbis(azanediyl))bis(3-methoxycyclobut-3-ene-1,2-dione)
_chemical_name_systematic        Sq-1,4-dimer
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-02-26 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.535(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4828(16)
_cell_length_b                   12.528(2)
_cell_length_c                   6.6496(11)
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.5550
_cell_measurement_theta_min      2.8890
_cell_volume                     706.0(2)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  69.50   0.50    8.00    --  -20.00   0.00  36.00  359
  2  ω    -70.00 -36.00   0.50    8.00    --  -20.00 -72.00 -36.00   68
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0477730000
_diffrn_orient_matrix_UB_12      0.0424282000
_diffrn_orient_matrix_UB_13      -0.0385813000
_diffrn_orient_matrix_UB_21      0.0099960000
_diffrn_orient_matrix_UB_22      -0.0186373000
_diffrn_orient_matrix_UB_23      -0.0993259000
_diffrn_orient_matrix_UB_31      -0.0680032000
_diffrn_orient_matrix_UB_32      -0.0325303000
_diffrn_orient_matrix_UB_33      0.0066367000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2742
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.958
_diffrn_reflns_theta_max         24.957
_diffrn_reflns_theta_min         2.902
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/ACN/CHCl3'
_exptl_crystal_size_max          0.0411
_exptl_crystal_size_mid          0.0321
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0954
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1908P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2552
_refine_ls_wR_factor_ref         0.2825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                865
_reflns_number_total             1223
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00623a2.cif
_cod_data_source_block           gnp-ab-1-4-dimer_mo
_cod_depositor_comments
'Adding full bibliography for 7243068--7243072.cif.'
_cod_database_code               7243068
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 88.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.996
_oxdiff_exptl_absorpt_empirical_full_min 0.739
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6587(3) 0.6361(2) 0.3045(4) 0.0290(8) Uani 1 1 d . . . . .
O2 O 0.5132(3) 0.62873(17) 0.7593(4) 0.0284(8) Uani 1 1 d . . . . .
O3 O 0.1603(3) 0.6168(2) 0.5378(4) 0.0326(9) Uani 1 1 d . . . . .
N4 N 0.3166(4) 0.6234(2) 0.0965(5) 0.0247(9) Uani 1 1 d . . . . .
H4 H 0.385026 0.627013 0.000994 0.030 Uiso 1 1 calc R . . . .
C2 C 0.5192(4) 0.6313(2) 0.3839(6) 0.0208(9) Uani 1 1 d . . . . .
C5 C 0.3694(4) 0.6244(2) 0.2846(6) 0.0223(9) Uani 1 1 d . . . . .
C3 C 0.4595(4) 0.6281(2) 0.5837(6) 0.0241(10) Uani 1 1 d . . . . .
C7 C 0.0860(4) 0.5026(3) 0.0381(5) 0.0263(10) Uani 1 1 d . . . . .
H7A H 0.095626 0.473468 0.176474 0.032 Uiso 1 1 calc R . . . .
H7B H 0.151053 0.457967 -0.048824 0.032 Uiso 1 1 calc R . . . .
C4 C 0.2948(4) 0.6219(3) 0.4833(6) 0.0243(9) Uani 1 1 d . . . . .
C6 C 0.1473(4) 0.6163(3) 0.0384(6) 0.0261(10) Uani 1 1 d . . . . .
H6A H 0.129279 0.647156 -0.097799 0.031 Uiso 1 1 calc R . . . .
H6B H 0.086956 0.659460 0.133140 0.031 Uiso 1 1 calc R . . . .
C1 C 0.7883(4) 0.6673(4) 0.4437(6) 0.0382(11) Uani 1 1 d . . . . .
H1A H 0.886420 0.634385 0.401974 0.057 Uiso 1 1 calc GR . . . .
H1B H 0.766024 0.643303 0.579830 0.057 Uiso 1 1 calc GR . . . .
H1C H 0.799471 0.745147 0.442841 0.057 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 115.0(3) . . ?
C5 N4 H4 118.7 . . ?
C5 N4 C6 122.6(3) . . ?
C6 N4 H4 118.7 . . ?
O1 C2 C5 128.5(3) . . ?
O1 C2 C3 136.7(3) . . ?
C5 C2 C3 94.8(3) . . ?
N4 C5 C2 135.4(3) . . ?
N4 C5 C4 134.9(3) . . ?
C2 C5 C4 89.7(3) . . ?
O2 C3 C2 137.8(4) . . ?
O2 C3 C4 135.0(3) . . ?
C2 C3 C4 87.2(3) . . ?
C7 C7 H7A 109.4 3_565 . ?
C7 C7 H7B 109.4 3_565 . ?
H7A C7 H7B 108.0 . . ?
C6 C7 C7 111.4(3) . 3_565 ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
O3 C4 C5 135.0(4) . . ?
O3 C4 C3 136.7(4) . . ?
C5 C4 C3 88.3(3) . . ?
N4 C6 C7 112.8(3) . . ?
N4 C6 H6A 109.0 . . ?
N4 C6 H6B 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.318(4) . ?
O1 C1 1.458(4) . ?
O2 C3 1.235(4) . ?
O3 C4 1.213(4) . ?
N4 H4 0.8800 . ?
N4 C5 1.310(5) . ?
N4 C6 1.473(5) . ?
C2 C5 1.409(5) . ?
C2 C3 1.443(5) . ?
C5 C4 1.491(5) . ?
C3 C4 1.524(5) . ?
C7 C7 1.525(7) 3_565 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.516(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C5 N4 -2.3(6) . . . . ?
O1 C2 C5 C4 179.3(3) . . . . ?
O1 C2 C3 O2 0.3(7) . . . . ?
O1 C2 C3 C4 -179.1(4) . . . . ?
O2 C3 C4 O3 1.0(6) . . . . ?
O2 C3 C4 C5 -178.7(4) . . . . ?
N4 C5 C4 O3 1.2(6) . . . . ?
N4 C5 C4 C3 -179.1(3) . . . . ?
C2 C5 C4 O3 179.6(4) . . . . ?
C2 C5 C4 C3 -0.7(2) . . . . ?
C2 C3 C4 O3 -179.6(4) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C5 N4 C6 C7 -82.9(4) . . . . ?
C5 C2 C3 O2 178.6(4) . . . . ?
C5 C2 C3 C4 -0.7(2) . . . . ?
C3 C2 C5 N4 179.1(3) . . . . ?
C3 C2 C5 C4 0.7(2) . . . . ?
C7 C7 C6 N4 -175.6(3) 3_565 . . . ?
C6 N4 C5 C2 -179.2(3) . . . . ?
C6 N4 C5 C4 -1.5(5) . . . . ?
C1 O1 C2 C5 166.5(3) . . . . ?
C1 O1 C2 C3 -15.5(5) . . . . ?
